Water → 1-(5-Bromopyridin-3-yl)propan-2-one
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:13]=1)[C:7](N(OC)C)=O.[CH2:14]([Mg]Cl)[CH3:15].[OH2:18]>C1COCC1>[Br:1][C:2]1[CH:13]=[C:6]([CH2:7][C:14](=[O:18])[CH3:15])[CH:5]=[N:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
44 g (180 mmol) of 5-bromo-N-methoxy-N-methylnicotinamide are dissolved in 200 mL of THF and 60 mL (180 mmol) of ethylmagnesium chloride solution (3M in ethyl ether) are added dropwise. The reaction medium is stirred at room temperature for one hour, poured into water and extracted with ethyl acetate. The organic phase is separated out after settling, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (70/30). 4 g (11%) of 1-(5-bromo-3-pyridyl)propanone are collected.